Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2023-02-21 17:18:27 UTC
HMDB IDHMDB0015253
Secondary Accession Numbers
  • HMDB15253
Metabolite Identification
Common NamePhenacemide
DescriptionPhenacemide is only found in individuals that have used or taken this drug. It is used to control certain seizures in the treatment of epilepsy. This medicine acts on the central nervous system (CNS) to reduce the number and severity of seizures. Phenacemide binds to and blocks neuronal sodium channels or voltage sensitive calcium channels. This blocks or suppresses neuronal depolarization and hypersynchronization. Hypersynchronization is what often causes seizures.
Structure
Data?1676999907
Synonyms
ValueSource
PhenuroneKegg
Carbamide phenylacetateHMDB
PhenacetylcarbamideHMDB
PhenacetylureaHMDB
PhenylacetylureaHMDB
PhenylacetylureeHMDB
PhenuronHMDB
(Phenylacetyl)ureaHMDB
Chemical FormulaC9H10N2O2
Average Molecular Weight178.1879
Monoisotopic Molecular Weight178.074227574
IUPAC Name(2-phenylacetyl)urea
Traditional Namephenacemide
CAS Registry Number63-98-9
SMILES
NC(=O)NC(=O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H10N2O2/c10-9(13)11-8(12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H3,10,11,12,13)
InChI KeyXPFRXWCVYUEORT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetamides
Direct ParentPhenylacetamides
Alternative Parents
Substituents
  • Phenylacetamide
  • N-acyl urea
  • Ureide
  • Dicarboximide
  • Carbonic acid derivative
  • Urea
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point215 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.06 g/LNot Available
LogP0.8Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available128.347http://allccs.zhulab.cn/database/detail?ID=AllCCS00000759
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.06 g/LALOGPS
logP0.81ALOGPS
logP0.46ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)11.75ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.19 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.43 m³·mol⁻¹ChemAxon
Polarizability17.49 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.75931661259
DarkChem[M-H]-136.31531661259
DeepCCS[M+H]+136.02730932474
DeepCCS[M-H]-133.44330932474
DeepCCS[M-2H]-169.20530932474
DeepCCS[M+Na]+144.04830932474
AllCCS[M+H]+138.432859911
AllCCS[M+H-H2O]+134.232859911
AllCCS[M+NH4]+142.432859911
AllCCS[M+Na]+143.532859911
AllCCS[M-H]-137.632859911
AllCCS[M+Na-2H]-138.432859911
AllCCS[M+HCOO]-139.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhenacemideNC(=O)NC(=O)CC1=CC=CC=C13009.5Standard polar33892256
PhenacemideNC(=O)NC(=O)CC1=CC=CC=C11406.5Standard non polar33892256
PhenacemideNC(=O)NC(=O)CC1=CC=CC=C11788.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenacemide,1TMS,isomer #1C[Si](C)(C)NC(=O)NC(=O)CC1=CC=CC=C11882.7Semi standard non polar33892256
Phenacemide,1TMS,isomer #1C[Si](C)(C)NC(=O)NC(=O)CC1=CC=CC=C11707.1Standard non polar33892256
Phenacemide,1TMS,isomer #1C[Si](C)(C)NC(=O)NC(=O)CC1=CC=CC=C12616.5Standard polar33892256
Phenacemide,1TMS,isomer #2C[Si](C)(C)N(C(N)=O)C(=O)CC1=CC=CC=C11752.5Semi standard non polar33892256
Phenacemide,1TMS,isomer #2C[Si](C)(C)N(C(N)=O)C(=O)CC1=CC=CC=C11775.2Standard non polar33892256
Phenacemide,1TMS,isomer #2C[Si](C)(C)N(C(N)=O)C(=O)CC1=CC=CC=C12606.9Standard polar33892256
Phenacemide,2TMS,isomer #1C[Si](C)(C)N(C(=O)NC(=O)CC1=CC=CC=C1)[Si](C)(C)C1924.7Semi standard non polar33892256
Phenacemide,2TMS,isomer #1C[Si](C)(C)N(C(=O)NC(=O)CC1=CC=CC=C1)[Si](C)(C)C1886.9Standard non polar33892256
Phenacemide,2TMS,isomer #1C[Si](C)(C)N(C(=O)NC(=O)CC1=CC=CC=C1)[Si](C)(C)C2482.2Standard polar33892256
Phenacemide,2TMS,isomer #2C[Si](C)(C)NC(=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C1842.0Semi standard non polar33892256
Phenacemide,2TMS,isomer #2C[Si](C)(C)NC(=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C1849.4Standard non polar33892256
Phenacemide,2TMS,isomer #2C[Si](C)(C)NC(=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C2320.9Standard polar33892256
Phenacemide,3TMS,isomer #1C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)C(=O)N([Si](C)(C)C)[Si](C)(C)C1867.4Semi standard non polar33892256
Phenacemide,3TMS,isomer #1C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)C(=O)N([Si](C)(C)C)[Si](C)(C)C2015.9Standard non polar33892256
Phenacemide,3TMS,isomer #1C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)C(=O)N([Si](C)(C)C)[Si](C)(C)C2142.9Standard polar33892256
Phenacemide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)NC(=O)CC1=CC=CC=C12114.8Semi standard non polar33892256
Phenacemide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)NC(=O)CC1=CC=CC=C11952.9Standard non polar33892256
Phenacemide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)NC(=O)CC1=CC=CC=C12632.5Standard polar33892256
Phenacemide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(N)=O)C(=O)CC1=CC=CC=C11986.4Semi standard non polar33892256
Phenacemide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(N)=O)C(=O)CC1=CC=CC=C11993.9Standard non polar33892256
Phenacemide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(N)=O)C(=O)CC1=CC=CC=C12687.1Standard polar33892256
Phenacemide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)NC(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2353.0Semi standard non polar33892256
Phenacemide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)NC(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2293.2Standard non polar33892256
Phenacemide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)NC(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2555.1Standard polar33892256
Phenacemide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2278.5Semi standard non polar33892256
Phenacemide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2259.1Standard non polar33892256
Phenacemide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2495.1Standard polar33892256
Phenacemide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2531.7Semi standard non polar33892256
Phenacemide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2561.4Standard non polar33892256
Phenacemide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2472.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phenacemide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-1bdb50bda427a0a6b7592017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenacemide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00kf-9200000000-38554ddfe2ad3808dc2a2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenacemide 10V, Positive-QTOFsplash10-004i-2900000000-bbe6000c85c6e7cad8d72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenacemide 20V, Positive-QTOFsplash10-014u-4900000000-65aecc6405e7dc3960db2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenacemide 40V, Positive-QTOFsplash10-0006-9100000000-470744c360a51861385e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenacemide 10V, Negative-QTOFsplash10-000x-7900000000-33581cec0b1c89a374a12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenacemide 20V, Negative-QTOFsplash10-000x-7900000000-c6b59b20b89c19c877592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenacemide 40V, Negative-QTOFsplash10-0006-9100000000-812937333ee84aac004a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenacemide 10V, Positive-QTOFsplash10-00kf-9600000000-eb2dcdcc261eec29fa082021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenacemide 20V, Positive-QTOFsplash10-0006-9100000000-6f93f0492b5f066950572021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenacemide 40V, Positive-QTOFsplash10-0006-9000000000-d3ddfb9a0b95dad2b0262021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenacemide 10V, Negative-QTOFsplash10-0006-9000000000-2cca984c3d943209d9fe2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenacemide 20V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenacemide 40V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01121 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01121 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01121
Phenol Explorer Compound IDNot Available
FooDB IDFDB007356
KNApSAcK IDNot Available
Chemspider ID4589
KEGG Compound IDC07428
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenacemide
METLIN IDNot Available
PubChem Compound4753
PDB IDNot Available
ChEBI ID183000
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Coker SB: The use of phenacemide for intractable partial complex epilepsy in children. Pediatr Neurol. 1986 Jul-Aug;2(4):230-2. [PubMed:3508693 ]
  2. Coker SB, Holmes EW, Egel RT: Phenacemide therapy of complex partial epilepsy in children: determination of plasma drug concentrations. Neurology. 1987 Dec;37(12):1861-6. [PubMed:3683877 ]

Enzymes

General function:
Involved in ion channel activity
Specific function:
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient
Gene Name:
SCN1A
Uniprot ID:
P35498
Molecular weight:
228969.5
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Wong MG, Defina JA, Andrews PR: Conformational analysis of clinically active anticonvulsant drugs. J Med Chem. 1986 Apr;29(4):562-72. [PubMed:3959032 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]